Penicillins having an imino substituted piperazindioncarbonylamino acyl sidechain

Abstract

Penicillins of the formula ##STR1## wherein R is hydrogen , sodium, potassium or certain ester groups; R 1 is in the α-configuration and is hydrogen or methoxy; R 2 is hydrogen, lower aklkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl, furyl, or pyridyl, or 2-amino-4-thiazolyl; R 3 is lower alkyl or substituted or unsubstituted phenyl, benzyl, phenethyl, thienyl or furyl; and R 4 is hydrogen or lower alkyl; are disclosed. These compounds possess useful antibacterial activity.

What is claimed is: 
     
       1. A compound of the formula: ##STR124## wherein R is hydrogen, sodium, potassium, t-butyl, benzyl, p-methoxybenzyl, p-nitrobenzyl, diphenylmethyl, 2,2,2-trichloroethyl, trimethylsilyl, --CH 2  --O--lower alkyl, ##STR125## R 1  is in the α-configuration and is hydrogen or methoxy; R 2  is hydrogen, lower alkyl, cycloalkyl, cycloalkenyl, cycloalkadienyl, ##STR126## R 3  is lower alkyl, ##STR127## R 4  is hydrogen or lower alkyl; R 5  is hydrogen or lower alkyl; R 6  is hydrogen, methyl, ethyl, methoxy, ethoxy, hydroxy, Cl or Br; m is zero, one or two; A is O or S; and R 7  is hydrogen, methyl, ethyl, Cl, or Br. 
     
     
       2. The compound of claim 1 wherein R is hydrogen, sodium, or potassium; R 1  is hydrogen; R 2  is phenyl, 4-hydroxyphenyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, or 2-amino-4-thiazolyl; R 3  is methyl, phenyl, 2-thienyl or 2-furyl; and R 4  is hydrogen or methyl. 
     
     
       3. The compound of claim 2 wherein R 3  is phenyl and R 4  is hydrogen. 
     
     
       4. The compound of claim 3 wherein R 2  is phenyl. 
     
     
       5. The compound of claim 4, 6β-[[D-[[[2,3-dioxo-4-[(phenylmethylene)amino]-1-piperazinyl]carbonyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. 
     
     
       6. The sodium slat of the compound of claim 5. 
     
     
       7. An antibacterial pharmaceutical composition comprising a pharmaceutically acceptable carrier and one or more antibacterially active compounds of the formula: ##STR128## wherein R is hydrogen, sodium, potassium; --CH 2  --O-lower alkyl, ##STR129## and R 1 , R 2 , R 3 , R 4 , and R 5   are as defined in claim 1. 
     
     
       8. The method of treating bacterial infections in mammals which comprises administering an effective amount of the composition of claim 7.